4-(2-Sulfanyl­idene-1,3-benzothia­zol-3-yl)butan-2-one

Du, C.-J.

doi:10.1107/S1600536810048051

organic compounds

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Volume 66| Part 12| December 2010| Page o3317

https://doi.org/10.1107/S1600536810048051

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4-(2-Sulfanylidene-1,3-benzothiazol-3-yl)butan-2-one

Chao-Jun Du ^a ^*

^aSchool of Biology and Chemical Engineering, Nanyang Institute of Technology, Nanyang 473004, People's Republic of China
^*Correspondence e-mail: chjdu@yahoo.com.cn

(Received 2 November 2010; accepted 18 November 2010; online 27 November 2010)

In the title compound, C₁₁H₁₁NOS₂, the benzine ring is coplanar with the thiazole ring, making a dihedral angle of 0.81 (1)°. In the crystal, adjacent molecules are connected into a helical chain along the b axis by S⋯S contacts [3.4345 (18) Å]. These helical chains are further assembled into a three-dimensional supermolecular network by intermolecular C—H⋯O hydrogen bond between aromatic ring H atoms and carbonyl groups.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 ). For a related structure, see: Zhu et al. (2009 ). For S⋯S contacts, see: Dai et al. (1997 ).

Experimental

Crystal data

C₁₁H₁₁NOS₂
M_r = 237.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.9457 (19) Å
b = 11.586 (4) Å
c = 19.830 (7) Å
V = 1136.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 296 K
0.23 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.905, T_max = 0.936
12565 measured reflections
1476 independent reflections
1176 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.07
1476 reflections
120 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1ⁱ	0.96	2.60	3.541 (5)	167
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048051/ds2068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048051/ds2068Isup2.hkl

checkCIF report

Related literature top

For a description of the Cambridge Structural Database, see: Allen (2002). For a related structure, see: Zhu et al. (2009). For S···S contacts, see: Dai et al. (1997).

Experimental top

A solution of benzothiazole-2-thiol (167.2 mg, 1.00 mmol) and in acetone (15 ml) was slowly added to a solution of CH₂Cl₂(170.0 mg, 2.00 mmol) in acetone (15 ml). The resultant solution was stirred and refluxed for 16 h and then filtered. Colorless crystals suitable for X-ray diffraction were obtained in about two weeks by slow diffusion of diethyl ether into a dilute solution of the title compound in methanol. yield: ca 35.8% (based on benzothiazole-2-thiol).

Structure description top

For a description of the Cambridge Structural Database, see: Allen (2002). For a related structure, see: Zhu et al. (2009). For S···S contacts, see: Dai et al. (1997).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. View of right-handle helical chain connected by S···S contacts along b axis.
	Fig. 3. View of three-dimensional supermolecular network connected by S···S contacts and C—H···O hydrogen bonds along the c direction.

4-(2-Sulfanylidene-1,3-benzothiazol-3-yl)butan-2-one top

Crystal data top

C₁₁H₁₁NOS₂	F(000) = 496
M_r = 237.33	D_x = 1.387 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2911 reflections
a = 4.9457 (19) Å	θ = 2.7–22.7°
b = 11.586 (4) Å	µ = 0.44 mm⁻¹
c = 19.830 (7) Å	T = 296 K
V = 1136.3 (7) Å³	Block, colorless
Z = 4	0.23 × 0.19 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	1476 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −6→6
T_min = 0.905, T_max = 0.936	k = −14→14
12565 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0535P)² + 0.413P] where P = (F_o² + 2F_c²)/3
1476 reflections	(Δ/σ)_max < 0.001
120 parameters	Δρ_max = 0.27 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₁H₁₁NOS₂	V = 1136.3 (7) Å³
M_r = 237.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.9457 (19) Å	µ = 0.44 mm⁻¹
b = 11.586 (4) Å	T = 296 K
c = 19.830 (7) Å	0.23 × 0.19 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	1476 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1176 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.936	R_int = 0.036
12565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	2 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
1476 reflections	Δρ_min = −0.31 e Å⁻³
120 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.4190 (4)	−0.16020 (16)	0.16706 (8)	0.0559 (8)
C3	0.5987 (5)	−0.25022 (15)	0.15525 (10)	0.0688 (10)
H3	0.6161	−0.3094	0.1866	0.083*
C4	0.7524 (5)	−0.25173 (19)	0.09657 (12)	0.0762 (11)
H4	0.8726	−0.3120	0.0887	0.091*
C5	0.7264 (5)	−0.1632 (2)	0.04970 (10)	0.0727 (10)
H5	0.8293	−0.1642	0.0104	0.087*
C6	0.5468 (5)	−0.07320 (17)	0.06150 (9)	0.0635 (9)
H6	0.5294	−0.0140	0.0301	0.076*
C7	0.3931 (4)	−0.07169 (15)	0.12018 (10)	0.0517 (8)
S1	0.2105 (2)	−0.13581 (7)	0.23522 (4)	0.0652 (2)
S2	−0.1380 (2)	0.07257 (8)	0.23950 (6)	0.0796 (3)
O1	0.0395 (7)	0.3256 (2)	0.04435 (16)	0.0938 (9)
N1	0.2077 (6)	0.0109 (2)	0.13995 (13)	0.0527 (6)
C1	0.0920 (7)	−0.0080 (3)	0.20141 (17)	0.0563 (8)
C8	0.1402 (8)	0.1127 (2)	0.09994 (17)	0.0595 (9)
H8A	−0.0493	0.1312	0.1064	0.071*
H8B	0.1670	0.0953	0.0526	0.071*
C9	0.3097 (8)	0.2163 (3)	0.11870 (18)	0.0604 (9)
H9A	0.2941	0.2295	0.1668	0.072*
H9B	0.4978	0.1995	0.1089	0.072*
C10	0.2300 (5)	0.3236 (2)	0.08225 (17)	0.0677 (7)
C11	0.3976 (7)	0.4283 (2)	0.09581 (18)	0.0677 (7)
H11A	0.3297	0.4919	0.0699	0.102*
H11B	0.5818	0.4132	0.0833	0.102*
H11C	0.3892	0.4469	0.1429	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0587 (19)	0.0440 (15)	0.0651 (18)	−0.0037 (15)	−0.0112 (17)	−0.0018 (14)
C3	0.071 (2)	0.0540 (17)	0.081 (2)	0.0062 (19)	−0.015 (2)	0.0014 (18)
C4	0.066 (2)	0.0627 (19)	0.100 (3)	0.010 (2)	−0.004 (2)	−0.011 (2)
C5	0.068 (2)	0.069 (2)	0.081 (2)	−0.005 (2)	0.008 (2)	−0.0089 (19)
C6	0.064 (2)	0.0609 (18)	0.066 (2)	−0.0031 (19)	−0.0016 (18)	0.0002 (17)
C7	0.0539 (19)	0.0446 (14)	0.0566 (16)	−0.0047 (15)	−0.0070 (16)	−0.0022 (13)
S1	0.0826 (6)	0.0508 (4)	0.0623 (4)	−0.0036 (5)	−0.0010 (5)	0.0044 (4)
S2	0.0827 (7)	0.0613 (5)	0.0950 (6)	−0.0010 (5)	0.0162 (6)	−0.0161 (5)
O1	0.0917 (17)	0.0742 (15)	0.115 (2)	0.0104 (17)	−0.0352 (14)	0.0259 (16)
N1	0.0536 (15)	0.0448 (12)	0.0598 (14)	−0.0007 (13)	−0.0075 (14)	0.0015 (11)
C1	0.0573 (19)	0.0456 (15)	0.0659 (18)	−0.0085 (16)	−0.0055 (18)	−0.0084 (14)
C8	0.058 (2)	0.0501 (15)	0.0710 (19)	0.0005 (16)	−0.0130 (17)	0.0067 (15)
C9	0.055 (2)	0.0501 (16)	0.076 (2)	0.0044 (17)	−0.0083 (19)	0.0091 (15)
C10	0.0791 (17)	0.0570 (12)	0.0671 (14)	0.0039 (15)	−0.0077 (12)	0.0097 (12)
C11	0.0791 (17)	0.0570 (12)	0.0671 (14)	0.0039 (15)	−0.0077 (12)	0.0097 (12)

Geometric parameters (Å, º) top

C2—C3	1.3900	O1—C10	1.206 (4)
C2—C7	1.3900	N1—C1	1.364 (4)
C2—S1	1.724 (2)	N1—C8	1.460 (4)
C3—C4	1.3900	C8—C9	1.511 (4)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.3900	C8—H8B	0.9700
C4—H4	0.9300	C9—C10	1.491 (4)
C5—C6	1.3900	C9—H9A	0.9700
C5—H5	0.9300	C9—H9B	0.9700
C6—C7	1.3900	C10—C11	1.494 (4)
C6—H6	0.9300	C11—H11A	0.9600
C7—N1	1.382 (3)	C11—H11B	0.9600
S1—C1	1.728 (3)	C11—H11C	0.9600
S2—C1	1.654 (4)

C3—C2—C7	120.0	N1—C1—S1	110.0 (2)
C3—C2—S1	129.62 (11)	S2—C1—S1	122.7 (2)
C7—C2—S1	110.38 (11)	N1—C8—C9	112.4 (3)
C4—C3—C2	120.0	N1—C8—H8A	109.1
C4—C3—H3	120.0	C9—C8—H8A	109.1
C2—C3—H3	120.0	N1—C8—H8B	109.1
C3—C4—C5	120.0	C9—C8—H8B	109.1
C3—C4—H4	120.0	H8A—C8—H8B	107.9
C5—C4—H4	120.0	C10—C9—C8	113.4 (3)
C4—C5—C6	120.0	C10—C9—H9A	108.9
C4—C5—H5	120.0	C8—C9—H9A	108.9
C6—C5—H5	120.0	C10—C9—H9B	108.9
C7—C6—C5	120.0	C8—C9—H9B	108.9
C7—C6—H6	120.0	H9A—C9—H9B	107.7
C5—C6—H6	120.0	O1—C10—C9	121.6 (2)
N1—C7—C6	127.51 (16)	O1—C10—C11	122.1 (3)
N1—C7—C2	112.49 (16)	C9—C10—C11	116.3 (3)
C6—C7—C2	120.0	C10—C11—H11A	109.5
C2—S1—C1	92.25 (14)	C10—C11—H11B	109.5
C1—N1—C7	114.8 (2)	H11A—C11—H11B	109.5
C1—N1—C8	121.3 (3)	C10—C11—H11C	109.5
C7—N1—C8	123.8 (3)	H11A—C11—H11C	109.5
N1—C1—S2	127.3 (3)	H11B—C11—H11C	109.5

C7—C2—C3—C4	0.0	C2—C7—N1—C1	1.5 (3)
S1—C2—C3—C4	−178.85 (17)	C6—C7—N1—C8	0.9 (4)
C2—C3—C4—C5	0.0	C2—C7—N1—C8	−179.6 (2)
C3—C4—C5—C6	0.0	C7—N1—C1—S2	−179.4 (2)
C4—C5—C6—C7	0.0	C8—N1—C1—S2	1.7 (5)
C5—C6—C7—N1	179.5 (2)	C7—N1—C1—S1	−1.8 (3)
C5—C6—C7—C2	0.0	C8—N1—C1—S1	179.3 (2)
C3—C2—C7—N1	−179.6 (2)	C2—S1—C1—N1	1.2 (2)
S1—C2—C7—N1	−0.53 (18)	C2—S1—C1—S2	178.9 (2)
C3—C2—C7—C6	0.0	C1—N1—C8—C9	85.9 (4)
S1—C2—C7—C6	179.05 (14)	C7—N1—C8—C9	−93.0 (3)
C3—C2—S1—C1	178.56 (17)	N1—C8—C9—C10	−175.5 (3)
C7—C2—S1—C1	−0.38 (15)	C8—C9—C10—O1	3.4 (5)
C6—C7—N1—C1	−178.0 (2)	C8—C9—C10—C11	−177.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1ⁱ	0.96	2.60	3.541 (5)	167

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NOS₂
M_r	237.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.9457 (19), 11.586 (4), 19.830 (7)
V (Å³)	1136.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.23 × 0.19 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.905, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	12565, 1476, 1176
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.07
No. of reflections	1476
No. of parameters	120
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1ⁱ	0.96	2.60	3.541 (5)	167

Symmetry code: (i) x+1, y, z.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dai, J., Munakata, M., Wu, L.-P., Kuroda-Sowa, T. & Suenaga, Y. (1997). Inorg. Chim. Acta, 258, 65–69. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, J.-Q., Fang, H.-C., Chen, B.-Y., Feng, M.-S. & Li, J.-N. (2009). Acta Cryst. E65, o1640. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3317

https://doi.org/10.1107/S1600536810048051

Open

access